KR20170030291A - Compound for organic electronic element, organic electronic element comprising the same, and electronic device thereof - Google Patents

Abstract

Disclosed are a compound represented by chemical formula 1, and an organic electrical device which includes a first electrode, a second electrode, and an organic layer between the first electrode and the second electrode. Also, disclosed is an electronic device including the same. By containing the compound represented by chemical formula 1 in the organic layer, it is possible to lower driving voltage of the organic electrical device, while lifespan and luminous efficiency increase.

Description

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a compound for an organic electronic device, an organic electronic device using the compound, and an electronic device using the compound.

TECHNICAL FIELD The present invention relates to a compound for an organic electric device, an organic electric device using the same, and an electronic device therefor.

In general, organic light emission phenomenon refers to a phenomenon in which an organic material is used to convert electric energy into light energy. An organic electric device using an organic light emitting phenomenon generally has a structure including an anode, an anode, and an organic material layer therebetween. Here, in order to increase the efficiency and stability of the organic electronic device, the organic material layer is often formed of a multilayer structure composed of different materials, and may be formed of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer.

A material used as an organic material layer in an organic electric device may be classified into a light emitting material and a charge transporting material such as a hole injecting material, a hole transporting material, an electron transporting material, and an electron injecting material depending on functions.

The light emitting material can be classified into a polymer type and a low molecular type depending on the molecular weight, and is classified into a phosphorescent material derived from singlet excited state of electrons and a phosphorescent material derived from the triplet excited state of electrons . Further, the light emitting material can be classified into blue, green, and red light emitting materials and yellow and orange light emitting materials required to realize better natural color depending on the luminescent color.

On the other hand, when only one material is used as a light emitting material, there arises a problem that the maximum light emission wavelength shifts to a long wavelength due to intermolecular interaction, the color purity decreases, or the efficiency of the device decreases due to the light emission attenuating effect. A host / dopant system may be used as a light emitting material in order to increase the light emitting efficiency through the light emitting layer. When the dopant having a smaller energy band gap than the host forming the light emitting layer is mixed with a small amount of the light emitting layer, the excitons generated in the light emitting layer are transported to the dopant to emit light with high efficiency. At this time, since the wavelength of the host is shifted to the wavelength band of the dopant, the desired wavelength light can be obtained depending on the type of the dopant used.

Currently, the portable display market is growing in size as a large-area display, which requires more power than the power consumption required by existing portable displays. Therefore, power consumption becomes a very important factor for portable displays, which have a limited power source, such as a battery, and efficiency and lifetime issues must be solved.

The efficiency, lifetime, and driving voltage are related to each other. As the efficiency increases, the driving voltage decreases. As the driving voltage decreases, the crystallization of the organic material due to Joule heating, which occurs during driving, And the lifetime tends to increase. However, simply improving the organic material layer can not maximize the efficiency. This is because, when the optimum combination of the energy level and the T ₁ value between the respective organic layers, and the intrinsic properties (mobility, interface characteristics, etc.) of the materials are achieved, long life and high efficiency can be achieved at the same time. Therefore, it is necessary to develop a light emitting material having high thermal stability and achieving a charge balance in the light emitting layer efficiently.

That is, in order to sufficiently exhibit the excellent characteristics of the organic electronic device, a material constituting the organic material layer in the device, such as a hole injecting material, a hole transporting material, a light emitting material, an electron transporting material and an electron injecting material is supported by a stable and efficient material However, the development of stable and efficient organic material layer materials for organic electroluminescent devices has not been sufficiently developed yet. Therefore, development of new materials is continuously required, and development of a host material for a light emitting layer is urgently required.

An object of the present invention is to provide a compound capable of lowering the driving voltage of a device and improving the luminous efficiency, color purity and lifetime of the device, an organic electric device using the same, and an electronic device therefor.

In one aspect, the invention provides compounds represented by the formula:

In another aspect, the present invention provides an organic electronic device using the compound represented by the above formula and an electronic device thereof.

By using the compound according to the embodiment of the present invention, not only the driving voltage of the device can be lowered, but also the luminous efficiency, color purity and lifetime of the device can be greatly improved.

BRIEF DESCRIPTION OF THE DRAWINGS FIG. 1 is an illustration of an organic electroluminescent device according to the present invention. FIG.

DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS Hereinafter, embodiments of the present invention will be described in detail with reference to the accompanying drawings.

It should be noted that, in adding reference numerals to the constituent elements of the drawings, the same constituent elements are denoted by the same reference numerals whenever possible, even if they are shown in different drawings. In the following description of the present invention, a detailed description of known functions and configurations incorporated herein will be omitted when it may make the subject matter of the present invention rather unclear.

In describing the components of the present invention, the terms first, second, A, B, (a), (b), and the like can be used. These terms are intended to distinguish the constituent elements from other constituent elements, and the terms do not limit the nature, order or order of the constituent elements. When a component is described as being "connected", "coupled", or "connected" to another component, the component may be directly connected to or connected to the other component, It should be understood that an element may be "connected," "coupled," or "connected."

In addition, when an element such as a layer, film, region, plate, or the like is referred to as being "on" or "on" another element, And the like. On the contrary, when an element is referred to as being "directly on " another element, it should be understood that it does not have another element in the middle.

As used in this specification and the appended claims, unless stated otherwise, the following terms have the following meanings:

The term " halo "or" halogen ", as used herein, unless otherwise indicated, is fluorine (F), bromine (Br), chlorine (Cl) or iodine (I).

As used herein, the term "alkyl" or "alkyl group " refers to a straight or branched Quot; means a radical of a saturated aliphatic group, including an alkyl group, a cycloalkyl-substituted alkyl group.

The term "haloalkyl group" or "halogenalkyl group" as used in the present invention means an alkyl group substituted with halogen unless otherwise stated.

The term "alkenyl group" or "alkynyl group ", as used herein, unless otherwise indicated, each have a double bond or triple bond of from 2 to 60 carbon atoms and include straight chain or branched chain groups, It is not.

The term "cycloalkyl" as used herein, unless otherwise specified, means alkyl which forms a ring having from 3 to 60 carbon atoms, but is not limited thereto.

The term "alkoxyl group "," alkoxy group ", or "alkyloxy group" used in the present invention means an alkyl group to which an oxygen radical is attached and, unless otherwise stated, has a carbon number of 1 to 60, It is not.

As used herein, the term "aryloxyl group" or "aryloxy group" refers to an aryl group attached to an oxygen radical and, unless otherwise stated, has a carbon number of 6 to 60, but is not limited thereto.

The term "fluorenyl group" or "fluorenylene group" used in the present invention means a monovalent or divalent functional group in which R, R 'and R & Substituted fluorenyl group "or" substituted fluorenylene group "means that at least one of the substituents R, R 'and R" is a substituent other than hydrogen, and R and R' Together with a spy compound.

The terms "aryl group" and "arylene group ", as used herein, unless otherwise specified, each have 6 to 60 carbon atoms, but are not limited thereto. In the present invention, the aryl group or the arylene group includes a single ring, a ring group, a plurality of ring systems bonded together, a spiro compound and the like.

The term "heterocyclic group" as used herein includes not only aromatic rings such as "heteroaryl group" or "heteroarylene group ", but also nonaromatic rings, Means a ring of 2 to 60 rings, but is not limited thereto. The term "heteroatom ", as used herein, unless otherwise indicated, refers to N, O, S, P, or Si, wherein the heterocyclic group includes single ring, ring, And the like.

The "heterocyclic group" may also include a ring containing SO ₂ in place of the carbon forming the ring. For example, the "heterocyclic group" includes the following compounds.

In the present specification, a monovalent or divalent functional group is referred to as a functional group name or a maleic acid is written in front of a parent compound. For example, "divalent benzothiophene" means a divalent functional group of a benzothiophene which is a parent compound, and similarly, "divalent dibenzothiophene" means a divalent functional group of a dibenzothiophene, Furan "refers to the bivalent functional group of the parent compound," bivalent dibenzofuran "refers to the divalent functional group of the dibenzofurane, which is the parent compound, and" bivalent pyrimidine "refers to the bivalent functional group of the parent compound, pyrimidine . Likewise, a trivalent functional group can be represented by a trivalent sign in front of the parent compound. For example, "trivalent aryl" represents a trivalent functional group of an aromatic group, and "trivalent fluorene" represents a trivalent functional group of a fluorene group.

As used herein, the term "ring" includes monocyclic and polycyclic rings, including hydrocarbon rings as well as heterocycles containing at least one heteroatom and including aromatic and non-aromatic rings.

As used herein, the term "polycyclic" includes ring assemblies such as biphenyl, terphenyl, and the like, as well as various fused ring systems and spiro compounds, including aromatic as well as non- The ring includes, of course, a heterocycle containing at least one heteroatom.

As used herein, the term "ring assemblies" means that two or more ring systems (a single ring or a fused ring system) are directly connected to each other through a single bond or a double bond, Means that the number of linkages is one less than the total number of rings in the compound. The ring assemblies may be directly connected to each other through a single bond or a double bond.

As used herein, the term " conjugated ring system "refers to a fused ring form shared by at least two atoms, in which the ring system of two or more hydrocarbons is conjugated and contains at least one heteroatom And at least one hetero ring system bonded thereto. Such conjugated ring systems may be aromatic rings, heteroaromatic rings, aliphatic rings or a combination of these rings.

The term "spiro compound" used in the present invention has a 'spiro union', and a spiro connection means a connection in which two rings share only one atom. In this case, the atoms shared in the two rings are called 'spyro atoms', and depending on the number of spyro atoms contained in one compound, they are referred to as' monospyros,' 'diospyros,' ' 'Compounds.

Also, if prefixes are named consecutively, it means that the substituents are listed in the order listed first. Means, for example, an alkoxy group substituted with an aryl group in the case of an arylalkoxy group, a carbonyl group substituted with an alkoxy group in the case of an alkoxycarbonyl group, and an alkenyl group substituted with an arylcarbonyl group in the case of an arylcarbonylalkenyl group, The arylcarbonyl group is a carbonyl group substituted with an aryl group.

In addition, a no explicit description, the terms used in this invention in the "unsubstituted or substituted", "substituted" is an alkyl group of deuterium, a halogen, an amino group, a nitrile group, a nitro _{group, C 1 -C 20, C 1} -C ₂₀ alkoxy group, C ₁ -C ₂₀ alkyl amine group, C ₁ -C ₂₀ alkyl thiophene group, C ₆ -C ₂₀ aryl thiophene group, C ₂ -C ₂₀ alkenyl, C ₂ -C of ₂₀ alkynyl, C ₃ -C ₂₀ cycloalkyl group, C ₆ -C ₂₀ aryl group, of a C ₆ -C ₂₀ aryl group substituted with a heavy hydrogen, C ₈ -C ₂₀ aryl alkenyl group, a silane group, a boron And a C ₂ -C ₂₀ heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P, and at least one substituent selected from the group consisting of a halogen atom, , And it is not limited to these substituents.

Unless otherwise expressly stated, the formula used in the present invention is applied in the same manner as the definition of the substituent by the definition of the index of the following formula.

When a is an integer of 0, substituent R ¹ is absent. When a is an integer of 1, one substituent R ¹ is bonded to any one of carbon atoms forming a benzene ring, and when a is an integer of 2 or 3 each coupled as follows: and wherein R ¹ may be the same or different from each other, a is the case of 4 to 6 integer, and bonded to the carbon of the benzene ring in a similar way, while the display of the hydrogen bonded to the carbon to form a benzene ring Is omitted.

1 is an exemplary view of an organic electroluminescent device according to an embodiment of the present invention.

1, an organic electroluminescent device 100 according to an embodiment of the present invention includes a first electrode 120, a second electrode 180 and a first electrode 120 formed on a substrate 110, And an organic material layer containing a compound according to the present invention is provided between the two electrodes 180. In this case, the first electrode 120 may be an anode and the second electrode 180 may be a cathode (cathode). In case of an inverting type, the first electrode may be a cathode and the second electrode may be an anode.

The organic material layer may include a hole injecting layer 130, a hole transporting layer 140, a light emitting layer 150, an electron transporting layer 160, and an electron injecting layer 170 sequentially on the first electrode 120. At this time, at least one of these layers may be omitted, or may further include a hole blocking layer, an electron blocking layer, a light emitting auxiliary layer 151, a buffer layer 141, etc., and the electron transporting layer 160 may serve as a hole blocking layer You can do it.

Also, although not shown, the organic electroluminescent device according to an embodiment of the present invention further includes a protective layer or a light-efficiency-improving layer formed on at least one surface of the first electrode and the second electrode opposite to the organic material layer can do.

The compound according to one embodiment of the present invention applied to the organic material layer may be a host or a dopant of the hole injection layer 130, the hole transport layer 140, the electron transport layer 160, the electron injection layer 170, It may be used as a material for the light-efficiency improvement layer. For example, the compound of the present invention may be used as the light emitting layer 150.

On the other hand, even if the core is the same core, since the band gap, the electrical characteristics, the interface characteristics, and the like can be changed depending on which substituent is bonded at which position, the selection of the core and the combination of the sub- In particular, when the optimal combination of the energy level and T ₁ value between the organic layers, and the intrinsic properties (mobility, interface characteristics, etc.) of the materials are achieved, long life and high efficiency can be achieved at the same time.

As described above, in order to solve the problem of light emission in the hole transporting layer in an organic electroluminescent device, it is preferable that a light-emitting auxiliary layer is formed between the hole transporting layer and the light emitting layer. It is necessary to develop different luminescence-assisting layers according to the above. On the other hand, in the case of the light-emission-assisting layer, it is difficult to deduce the characteristics of the organic layer to be used even if a similar core is used because the relationship between the hole-transport layer and the light-emitting layer (host)

Accordingly, in the present invention, by forming a phosphorescent host using the compound represented by the formula (1), the energy level and T ₁ value between each organic material layer, the intrinsic properties (mobility, interface characteristics, etc.) And efficiency can be improved at the same time.

An organic electroluminescent device according to an embodiment of the present invention may be manufactured using various deposition methods. For example, a metal or a metal oxide having conductivity or an alloy thereof may be deposited on a substrate to form a cathode 120, and a hole injection layer 130 may be formed thereon. A hole transport layer 140, a light emitting layer 150, an electron transport layer 160, and an electron injection layer 170, and then depositing a material that can be used as a cathode 180 on the organic layer. have. Further, a light emitting auxiliary layer 151 may be further formed between the hole transport layer 140 and the light emitting layer 150.

In addition, the organic material layer may be formed using a variety of polymer materials, not a vapor deposition method, or a solution process or a solvent process such as a spin coating process, a nozzle printing process, an inkjet printing process, a slot coating process, a dip coating process, It is possible to produce a smaller number of layers by a method such as a dipping process, a screen printing process, or a thermal transfer process. Since the organic material layer according to the present invention can be formed by various methods, the scope of the present invention is not limited by the forming method.

The organic electroluminescent device according to an embodiment of the present invention may be a front emission type, a back emission type, or a both-sided emission type, depending on the material used.

WOLED (White Organic Light Emitting Device) has advantages of high resolution realization and fairness, and can be manufactured using existing color filter technology of LCD. Various structures for a white organic light emitting device mainly used as a backlight device have been proposed and patented. Typically, a stacking method in which R (Red), G (Green) and B (Blue) light emitting parts are arranged side by side, and R, G and B light emitting layers are stacked up and down , And a color conversion material (CCM) method using photo-luminescence of an inorganic phosphor by using electroluminescence by a blue (B) organic light emitting layer and light from the electroluminescent material. Can be applied to such WOLED.

The organic electroluminescent device according to an embodiment of the present invention may be one of an organic electroluminescent device, an organic solar cell, an organophotoreceptor, an organic transistor, or a device for monochromatic or white illumination.

Another embodiment of the present invention can include an electronic device including a display device including the above-described organic electronic device of the present invention and a control unit for controlling the display device. The electronic device may be a current or future wired or wireless communication terminal and includes all electronic devices such as a mobile communication terminal such as a mobile phone, a PDA, an electronic dictionary, a PMP, a remote controller, a navigation device, a game machine, various TVs, and various computers.

Hereinafter, the compound according to one aspect of the present invention will be described.

A compound according to one aspect of the present invention is represented by the following formula (1).

≪ Formula 1 >

      &Lt; Formula 2 > < EMI ID =

Each symbol described in the above formula can be defined as follows.

In the above formulas,

A is one of the formulas (2) to (4)

X is -O- or -S-,

R ² to R ²³ independently of one another are hydrogen; heavy hydrogen; halogen; An aryl group of C ₆ -C ₆₀ ; A fluorenyl group; Heterocyclic group of _{O, N, S, C 2} -C 60 containing at least one heteroatom selected from the group consisting of Si and P; A C ₁ -C ₅₀ alkyl group; A fused ring group of a C ₆ -C ₆₀ aromatic ring and a C ₃ -C ₆₀ aliphatic ring; An alkenyl group of C ₂ -C ₂₀ ; A C ₁ -C ₃₀ alkoxyl group; And an aryloxy group of C ₆ -C ₃₀ .

Preferably, R ² to R ²³ independently of one another are hydrogen; heavy hydrogen; halogen; A C ₆ -C ₃₀ aryl group; A fluorenyl group; And a C ₂ -C ₃₀ heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P;

R ² to R ²³ may independently be bonded to each other to form at least one aromatic or heteroaromatic ring. R ² to R ²³ which do not form a ring may be the same or different, . Illustratively, R &lt; ¹⁰ &gt; and R &lt; ¹¹ &gt; or R &lt; ²² &gt; and R &lt; ²³ &gt; may bond to each other to form a ring such as naphthalene together with the benzene ring to which they are bonded.

또는

일 수 있다.R ¹ is

or

Lt; / RTI &gt;

L ¹ is a single bond; C ₆ -C ₆₀ arylene groups; A fluorenylene group; And a C ₂ -C ₆₀ heteroarylene group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P, and is preferably a single bond; A C ₆ -C ₃₀ arylene group; And a C ₂ -C ₃₀ heteroarylene group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P; Illustratively, L ¹ is a single bond, selected from the group consisting of phenylene, pyreneylene, naphthylene, biphenylene, pyridylene, pyrimidylene, triazinylene, quinazolylene, benzoquinazolinyl, benzothienopyrimidinyl, Benzoporpholimidinylene, carbazolylene, benzocarbazolylene, pyridoindolylene, benzoquinolylene, phenanthridinyl, and the like.

L ² is a C ₆ -C ₆₀ trivalent arylene group; A trivalent fluorenylene group; And a C ₂ -C ₆₀ trivalent heteroarylene group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P, and preferably L ² Is a C ₆ -C ₃₀ trivalent arylene group; A trivalent fluorenylene group; And a C ₂ -C ₃₀ trivalent heteroarylene group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P, and the like. Illustratively, L ² may be a trivalent phenylene, a trivalent pyridine, a trivalent pyrimidine, a trivalent triazine, or the like.

Ar ¹ and Ar ² are, independently of each other, a C ₆ -C ₆₀ aryl group; A fluorenyl group; A fused ring group of a C ₃ -C ₆₀ aliphatic ring and a C ₆ -C ₆₀ aromatic ring; Heterocyclic group of _{O, N, S, C 2} -C 60 containing at least one heteroatom selected from the group consisting of Si and P; And -L'-N (R _a ) (R _b ); Aryl group preferably, the Ar ¹ and Ar ² are independently of one another, C ₆ -C _60; A fluorenyl group; Heterocyclic group of _{O, N, S, C 2} -C 60 containing at least one heteroatom selected from the group consisting of Si and P; And -L'-N (R _a ) (R _b ); and more preferably, Ar ¹ and Ar ² are independently of each other a C ₆ -C ₃₀ aryl group; A fluorenyl group; Heterocyclic group of _{O, N, S, C 2} -C 30 containing at least one heteroatom selected from the group consisting of Si and P; And -L'-N (R _a ) (R _b ); Illustratively, Ar ¹ and Ar ² are, independently of each other, phenyl, naphthyl, phenanthryl, biphenyl, pyrenyl, tolyl, deuterium substituted phenyl, terphenyl, fluorenyl, triphenylene, Benzoquinolyl, benzyloxycarbonyl, benzyloxycarbonyl, benzyloxycarbonyl, benzyloxycarbonyl, benzyloxycarbonyl, benzyloxycarbonyl, benzyloxycarbonyl, benzyloxycarbonyl, benzyloxycarbonyl, benzyloxycarbonyl, benzyloxycarbonyl and the like.

L 'is a single bond; C ₆ -C ₆₀ arylene groups; A fluorenylene group; A fused ring group of a C ₃ -C ₆₀ aliphatic ring and a C ₆ -C ₆₀ aromatic ring; And a C ₂ -C ₆₀ heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P, and preferably L 'is a single bond A C ₆ -C ₃₀ arylene group; A fluorenylene group; And a C ₂ -C ₃₀ heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P, and the like. Illustratively, L 'may be a single bond, a phenylene group, or the like.

R _a and R _b are independently of each other a C ₆ -C ₆₀ aryl group; A fluorenyl group; A fused ring group of a C ₃ -C ₆₀ aliphatic ring and a C ₆ -C ₆₀ aromatic ring; And a C ₂ -C ₆₀ heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P, and preferably, R _a and R _b may be the same or different, Independently of each other, a C ₆ -C ₃₀ aryl group; A fluorenyl group; And a C ₂ -C ₃₀ heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P, and the like. Illustratively, R & lt _{; a} & gt _; and R &lt; _b & gt _; , independently of one another, may be phenyl, biphenyl, fluorenyl, naphthyl, and the like.

Herein, each of the aryl group, the fluorenyl group, the heterocyclic group, the fused ring group, the alkyl group, the alkenyl group, the alkoxyl group, the aryloxy group, the arylene group, the heteroarylene group and the fluorenylene group may be deuterium; halogen; A silane group; Siloxyl group; Boron group; Germanium group; Cyano; A nitro group; An alkyl thio group of C ₁ -C ₂₀ ; A C ₁ -C ₂₀ alkoxyl group; A C ₁ -C ₂₀ alkyl group; An alkenyl group of C ₂ -C ₂₀ ; A C ₂ -C ₂₀ alkynyl group; C ₆ -C ₂₀ An aryl group; A C ₆ -C ₂₀ aryl group substituted by deuterium; A fluorenyl group; A C ₂ -C ₂₀ heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P; A C ₃ -C ₂₀ cycloalkyl group; An arylalkyl group of C ₇ -C ₂₀ ; Aryl, and C ₈ -C ₂₀ alkenyl group of; may be further substituted with one or more substituents selected from the group consisting of, in the case where each of these substituents are adjacent, bond to one another to form a ring.

Specifically, the formula (1) may be represented by one of the following formulas (5) to (10).

&Lt; Formula 5 > < EMI ID =

&Lt; Formula 8 > < EMI ID =

In the above Chemical Formulas 5 to 10, X and R ¹ to R ²³ are the same as defined in Chemical Formulas 1 to 4.

The formula 1 may be represented by one of the following formulas 1-1 to 1-4.

&Lt; Formula 1-1 > < Formula 1-2 > < Formula 1-3 &

In Formulas 1-1 to 1-4, X, R ¹ to R ^9, and R ¹⁸ to R ²¹ are the same as defined in Formulas 1 to 4.

R ²⁴ to R ²⁷ independently from each other are hydrogen; heavy hydrogen; halogen; An aryl group of C ₆ -C ₆₀ ; A fluorenyl group; Heterocyclic group of _{O, N, S, C 2} -C 60 containing at least one heteroatom selected from the group consisting of Si and P; A C ₁ -C ₅₀ alkyl group; A fused ring group of a C ₆ to C ₆₀ aromatic ring and a C _{3 to} C ₆₀ aliphatic ring; An alkenyl group of C ₂ -C ₂₀ ; A C ₁ -C ₃₀ alkoxyl group; And a C ₆ -C ₃₀ aryloxy group.

Preferably, R ²⁴ to R ²⁷ independently from each other are hydrogen; heavy hydrogen; halogen; A C ₆ -C ₃₀ aryl group; A fluorenyl group; A C ₂ -C ₃₀ heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P, and the like.

Specifically, the compound represented by Formula 1 may be any one of the following compounds.

In another embodiment, the present invention provides a compound for an organic electroluminescent device represented by the general formula (1).

The organic electroluminescent device includes a first electrode; A second electrode; And an organic material layer disposed between the first electrode and the second electrode. The organic material layer may include a compound represented by Formula 1, wherein Formula 1 is a hole injecting layer, a hole transporting layer, Or the light-emitting layer. That is, the compound represented by the formula (1) can be used as a material for the hole injection layer, the hole transport layer, the light emission assisting layer or the light emitting layer. Preferably, the compound represented by the formula (1) can be used as a phosphorescent host material of the light emitting layer.

Specifically, the present invention provides an organic electronic device comprising one of the compounds represented by Chemical Formulas 5 to 10 or 1-1 to 1-4 in the organic material layer. Specifically, An organic electroluminescent device comprising the compound. The compound contained in the organic material layer may be a single compound or a mixture of two or more compounds represented by the general formula (1). For example, the light-emitting layer in the organic material layer may be formed solely of the P-1-1 compound or may include a mixture of P-1-1 and P-1-2.

In another embodiment of the present invention, the light efficiency improving layer is formed on at least one side of the one side of the first electrode opposite to the organic layer, or one side of the one side of the second electrode opposite to the organic layer, And an organic electroluminescent device.

Hereinafter, the synthesis examples of the compound represented by the formula (1) according to the present invention and the production examples of the organic electric device will be specifically described with reference to examples, but the present invention is not limited to the following examples.

Synthetic example

Illustratively, the compounds according to the invention (Final Products) are prepared by reacting Core and Sub 1 as shown in Scheme 1 below, but are not limited thereto.

&Lt; Reaction 1 > (Y: Br, Cl, I)

I. Synthesis of Core

1. Example of synthesis of Core 1

Synthesis of Core 1-a

Dibenzo [b, d] thiophen- 1-ylboronic acid (7 g, 30.69 mmol) in 2-bromobenzamide (6.14 g, 30.69 mmol), Pd (PPh 3) 4 (1.06 g, 0.92 mmol), K 2 CO 3 ( 12.73 g, 92.08 mmol), THF (100 ml) and H ₂ O (50 ml) were added, and the mixture was refluxed at 90 ° C for 6 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, extracted with ethyl acetate, and washed with water. The organic layer was dried over MgSO ₄ and concentrated. The resulting organic material was separated using a silicagel column to obtain 6.98 g (yield: 75%) of the product.

Synthesis of Core 1-b

Core 1-a (6.5 g, 21.43 mmol) in CuI (0.41 g, 2.14 mmol) , PPh 3 (1.12 g, 4.29 mmol), potassium tert-butoxide (KO-tBu) (4.81 g, 42.85 mmol), o- Add xylene (70 ml) and reflux at 120 ° C for 18 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, extracted with ethyl acetate, and washed with water. The organic layer was dried over MgSO ₄ and concentrated. The resulting organic material was separated using a silicagel column to obtain 5.81 g (yield: 90%) of the product.

Synthesis of Core 1-c

POCl ₃ (3.36 g, 21.90 mmol), N, N- diisopropylethylamine (DIEA) (1.89 g, 14.60 mmol) and toluene (70 ml) were added to Core 1-b (5.5 g, Reflux. When the reaction is complete, the temperature of the reaction is cooled to room temperature and poured into ice water. extracted with ethyl acetate and wiped with water. The organic layer is dried over MgSO ₄ and filtered through celite. The solvent was removed and the resulting solid was recrystallized and filtered to give 4.55 g (yield: 70%) of the product.

Synthesis of Core 1

To a solution of bis (pinacolato) diboron (5.65 g, 20.17 mmol), PdCl ₂ (dppf) ₂ (0.55 g, 0.67 mmol), KOAc (3.96 g, 40.34 mmol), DMF 50 ml), and the mixture is refluxed at 120 ° C for 6 hours. When the reaction was completed, the temperature of the reaction mixture was cooled to room temperature, extracted with MC and wiped with water. The organic layer was dried over MgSO ₄ and concentrated. The resulting organic material was separated using a silicagel column to obtain 4.42 g (yield: 80%) of the product.

2. Example of synthesis of Core 2

Synthesis of Core 2-a

Benzo [b] naphtho [2,1- d] thiophen-6-ylboronic acid (10 g, 35.96 mmol) 2-bromobenzamide (7.19 g, 35.96 mmol), Pd (PPh 3) 4 (1.25 g, 1.08 mmol) in 9.78 g (yield: 77%) of the product was obtained using the above Core 1-a synthesis method, K ₂ CO ₃ (14.91 g, 107.89 mmol), THF (100 ml) and H ₂ O (50 ml).

Synthesis of Core 2-b

To a solution of CuI (0.52 g, 2.74 mmol), PPh ₃ (1.44 g, 5.49 mmol), potassium tert-butoxide (KO-tBu) (6.16 g, 54.89 mmol) xylene (100 ml) was subjected to the synthesis of Core 1-b to obtain 8.87 g (yield: 92%) of the product.

Synthesis of Core 2-c

Of Core 2-b (8.5 g, 24.19 mmol) in _{POCl 3 (4.45 g, 29.03 mmol} ), N, N -diisopropylethylamine (DIEA) (2.50 g, 19.35 mmol), toluene (80 ml) to the Core-1 c 6.71 g (yield: 75%) of the product was obtained using the synthetic method.

Synthesis of Core 2

To a solution of bis (pinacolato) diboron (7.39 g, 26.36 mmol), PdCl ₂ (dppf) ₂ (0.72 g, 0.88 mmol), KOAc (5.17 g, 52.72 mmol), DMF 80 ml) was obtained 6.65 g (yield: 82%) of the product using the above Core 1 synthesis method.

3. Example of synthesis of Core 3

Synthesis of Core 3-a

Dibenzo [b, d] thiophen- 2-ylboronic acid (15 g, 65.77 mmol) in 2-bromobenzamide (13.16 g, 65.77 mmol), Pd (PPh 3) 4 (2.28 g, 1.97 mmol), K 2 CO 3 ( 16.16 g (yield: 81%) of the product was obtained using the Core 1-a synthesis method described above, from 27.27 g, 197.31 mmol), THF (200 ml) and H ₂ O (100 ml).

Synthesis of Core 3-b

To a solution of CuI (1.00 g, 5.27 mmol), PPh ₃ (2.77 g, 10.55 mmol), potassium tert-butoxide (KO-tBu) (11.84 g, 105.48 mmol) xylene (200 ml) was obtained 6.68 g (yield: 42%) of the product using the synthesis of Core 1-b.

Synthesis of Core 3-c

Of Core 3-b (6.5 g, 21.57 mmol) in _{POCl 3 (3.97 g, 25.88 mmol} ), N, N -diisopropylethylamine (DIEA) a (2.23 g, 17.26 mmol), toluene (70 ml) the Core 1-c 5.04 g (yield: 73%) of the product was obtained using the synthetic method.

Synthesis of Core 3

(4.64 g, 46.90 mmol), DMF (0.60 g, 0.78 mmol), PdCl ₂ (dppf) ₂ (0.64 g, 0.78 mmol), bis (pinacolato) diboron (6.57 g, 23.45 mmol), Core 3-c 80 ml) was obtained 4.89 g (yield: 76%) of the product using the above Core 1 synthesis method.

4. Synthesis example of Core 4

Synthesis of Core 4-a

Benzo [b] naphtho [2,1- d] thiophen-5-ylboronic acid (12 g, 43.15 mmol) 2-bromobenzamide (8.63 g, 43.15 mmol), Pd (PPh 3) 4 (1.50 g, 1.29 mmol) in 12.05 g (yield: 79%) of the product was obtained using the Core 1-a synthesis method, K ₂ CO ₃ (17.89 g, 129.44 mmol), THF (150 ml) and H ₂ O (70 ml).

Synthesis of Core 4-b

Core 4-a (12 g, 34.95 mmol) in CuI (0.65 g, 3.40 mmol) , PPh 3 (1.78 g, 6.79 mmol), potassium tert-butoxide (KO-tBu) (7.62 g, 67.90 mmol), o- xylene (150 ml) was obtained by using the above synthesis method of Core 1-b, yielding 10.62 g (yield: 89%) of the product.

Synthesis of Core 4-c

To the Core 4-b (10 g, 28.46 mmol), POCl ₃ (5.24 g, 34.15 mmol), N, Ndiisopropylethylamine (DIEA) (2.94 g, 22.76 mmol) 7.37 g (yield: 70%) of the product was obtained using the synthetic method.

Synthesis of Core 4

To a solution of bis (pinacolato) diboron (7.95 g, 28.39 mmol), PdCl ₂ (dppf) ₂ (0.77 g, 0.95 mmol), KOAc (5.57 g, 56.78 mmol), DMF 100 ml) was obtained 6.55 g (yield: 75%) of the product using the above Core 1 synthesis method.

5. Synthesis Example of Core 5

Synthesis of Core 5-b

To a solution of CuI (0.56 g, 2.97 mmol), PPh ₃ (1.56 g, 5.93 mmol), potassium tert-butoxide (KO-tBu) (6.66 g, 59.33 mmol) xylene (100 ml) was subjected to the synthesis of Core 1-b to obtain 3.84 g (yield: 43%) of the product.

Synthesis of Core 5-c

POCl ₃ (2.26 g, 14.73 mmol), N, N- diisopropylethylamine (DIEA) (1.27 g, 9.82 mmol) and toluene (50 ml) were added to Core 5-b (3.7 g, 12.28 mmol) 2.83 g (yield: 72%) of the product was obtained using the synthetic method.

Synthesis of Core 5

To a solution of bis (pinacolato) diboron (5.78 g, 20.64 mmol), PdCl ₂ (dppf) ₂ (0.56 g, 0.69 mmol), KOAc (4.05 g, 41.27 mmol), DMF 60 ml) was obtained 4.7 g (yield: 83%) of the product using the above-described synthesis of Core 1.

6. Example of synthesis of Core 6

Synthesis of Core 6-a

Dibenzo [b, d] thiophen- 3-ylboronic acid (25 g, 109.62 mmol) to 2-bromobenzamide (21.93 g, 109.62 mmol), Pd (PPh 3) 4 (3.80 g, 3.29 mmol), K 2 CO 3 ( 29.26 g (yield: 88%) of the product was obtained by using the Core 1-a synthesis method described above, 45.45 g, 328.85 mmol), THF (300 ml) and H ₂ O (150 ml).

Synthesis of Core 6-b

To a solution of CuI (1.82 g, 9.56 mmol), PPh ₃ (5.01 g, 19.12 mmol), potassium tert-butoxide (KO-tBu) (21.45 g, 191.18 mmol) xylene (300 ml) was subjected to the synthesis of Core 1-b to obtain 10.95 g (yield: 38%) of the product.

Synthesis of Core 6-c

Of Core 6-b (10.6 g, 35.17 mmol) in _{POCl 3 (6.47 g, 42.21 mmol} ), N, N -diisopropylethylamine (DIEA) (3.64 g, 28.14 mmol), a toluene (110 ml) the Core 1-c 7.65 g (yield: 68%) of the product was obtained using the synthetic method.

Synthesis of Core 6

To a solution of bis (pinacolato) diboron (10.12 g, 36.12 mmol), PdCl ₂ (dppf) ₂ (0.98 g, 1.20 mmol), KOAc (7.09 g, 72.23 mmol), DMF 100 ml) was used to obtain 8.42 g (yield: 85%) of the product using the above-described synthesis of Core 1.

7. Example of synthesis of Core 7

Synthesis of Core 7-a

Benzo [b] naphtho [1,2- d] thiophen-5-ylboronic acid (17 g, 61.12 mmol) 2-bromobenzamide (12.23 g, 61.12 mmol), Pd (PPh 3) 4 (2.12 g, 1.83 mmol) in 19.87 g (yield: 92%) of the product was obtained using the above Core 1-a synthesis method, K ₂ CO ₃ (25.34 g, 183.37 mmol), THF (200 ml) and H ₂ O (100 ml).

Synthesis of Core 7-b

To a solution of CuI (1.02 g, 5.38 mmol), PPh ₃ (2.82 g, 10.75 mmol), potassium tert-butoxide (KO-tBu) (12.06 g, 107.51 mmol) xylene (200 ml) was subjected to synthesis of Core 1-b to obtain 17.57 g (yield: 93%) of the product.

Synthesis of Core 7-c

POCl ₃ (6.81 g, 44.39 mmol), N, N- diisopropylethylamine (DIEA) (3.83 g, 29.59 mmol) and toluene (150 ml) were added to Core 1-c 8.89 g (yield: 65%) of the product was obtained using the synthetic method.

Synthesis of Core 7

To a solution of bis (pinacolato) diboron (10.00 g, 35.69 mmol), PdCl ₂ (dppf) ₂ (0.97 g, 1.19 mmol), KOAc (7.00 g, 71.38 mmol) in DMF (8.8 g, 23.79 mmol) 100 ml) was used to obtain 9.66 g (yield: 88%) of the product using the above-described synthesis of Core 1.

8. Example of synthesis of Core 8

Synthesis of Core 8-a

Benzo [b] naphtho [1,2- d] thiophen-6-ylboronic acid (14 g, 50.34 mmol) 2-bromobenzamide (10.07 g, 50.34 mmol), Pd (PPh 3) 4 (1.74 g, 1.51 mmol) in 15.66 g (yield: 88%) of the product was obtained using the Core 1-a synthesis method, K ₂ CO ₃ (20.87 g, 151.01 mmol), THF (200 ml) and H ₂ O (100 ml).

Synthesis of Core 8-b

To a solution of CuI (0.81 g, 4.24 mmol), PPh ₃ (2.23 g, 8.49 mmol), potassium tert-butoxide (KO-tBu) (9.52 g, 84.88 mmol) xylene (200 ml) was subjected to synthesis of Core 1-b to obtain 12.68 g (yield: 85%) of the product.

Synthesis of Core 8-c

Of Core 8-b (12 g, 34.15 mmol) in _{POCl 3 (6.28 g, 40.98 mmol} ), N, N -diisopropylethylamine (DIEA) (3.53 g, 27.32 mmol), a toluene (150 ml) the Core 1-c 8.46 g (yield: 67%) of the product was obtained using the synthetic method.

Synthesis of Core 8

To a solution of bis (pinacolato) diboron (9.32 g, 33.25 mmol), PdCl ₂ (dppf) ₂ (0.91 g, 1.11 mmol), KOAc (6.53 g, 66.51 mmol) in DMF (8.2 g, 22.17 mmol) 100 ml) was subjected to synthesis of Core 1 to obtain 9 g of product (yield: 88%).

9. Example of synthesis of Core 9

Synthesis of Core 9-a

Dibenzo [b, d] thiophen- 4-ylboronic acid (7.7 g, 33.76 mmol) in 2-bromobenzamide (6.75 g, 33.76 mmol), Pd (PPh 3) 4 (1.17 g, 1.01 mmol), K 2 CO 3 ( 14.0 g, 101.28 mmol), THF (100 ml) and H ₂ O (50 ml) were used to synthesize Core 1-a to obtain 8.5 g (yield: 83%) of the product.

Synthesis of Core 9-b

To a solution of CuI (0.51 g, 2.67 mmol), PPh ₃ (1.40 g, 5.34 mmol), potassium tert-butoxide (KO-tBu) (5.99 g, 53.40 mmol) xylene (100 ml) was used to synthesize Core 1-b to obtain 7 g (yield: 87%) of the product.

Synthesis of Core 9-c

POCl ₃ (5.49 g, 35.84 mmol), N, N- diisopropylethylamine (DIEA) (3.09 g, 23.89 mmol) and toluene (100 ml) were added to Core 9-b (9 g, 29.86 mmol) 7.35 g (yield: 77%) of the product was obtained using the synthetic method.

Synthesis of Core 9

To a solution of bis (pinacolato) diboron (9.33 g, 33.30 mmol), PdCl ₂ (dppf) ₂ (0.91 g, 1.11 mmol), KOAc (6.54 g, 66.60 mmol), DMF 90 ml) was obtained 7.4 g (yield: 81%) of the product using the above-described synthesis of Core 1.

10. Synthesis example of Core 10

Synthesis of Core 10-b

(1.44 g, 7.58 mmol), PPh ₃ (4.98 g, 15.16 mmol), potassium tert-butoxide (KO-tBu) (17.01 g, 151.63 mmol), o- xylene (250 ml) was used to synthesize 9.14 g (yield: 40%) of the product using the synthesis of Core 1-b.

Synthesis of Core 10-c

POCl ₃ (5.43 g, 35.44 mmol), N, N- diisopropylethylamine (DIEA) (3.05 g, 23.63 mmol) and toluene (100 ml) were added to Core 10-b (8.9 g, 29.53 mmol) 6.99 g (yield: 74%) of the product was obtained using the synthetic method.

Synthesis of Core 10

(7.88 g, 28.14 mmol), PdCl ₂ (dppf) ₂ (0.77 g, 0.94 mmol), KOAc (5.52 g, 56.28 mmol), DMF 100 ml) was obtained 6.64 g (yield: 86%) of the product using the above Core 1 synthesis method.

[Table 1]

Ⅱ. Example of Sub1

On the other hand, the compound belonging to Sub 1 may be, but not limited to, the following compounds, and Table 2 shows the FD-MS value of the compound belonging to Sub 1.

[Table 2]

III. Product synthesis

1. P-1-1 Synthetic example

Core 1 (5.5 g, 13.37 mmol ) sub 1-1 (3.58 g, 13.37 mmol), Pd (PPh 3) 4 (0.46 g, 0.40 mmol), K 2 CO 3 (5.54 g, 40.11 mmol) in, THF ( 60 ml) and H ₂ O (30 ml), and the mixture is refluxed at 90 ° C for 12 hours. When the reaction was completed, the temperature of the reaction mixture was cooled to room temperature, extracted with MC and wiped with water. The organic layer was dried over MgSO ₄ and concentrated. The resulting organic material was separated using a silicagel column to obtain 5.32 g (yield: 77%) of the product.

2. P-2-1 Synthetic example

Core 2 sub 1-1 (2.15 g, 8.02 mmol), Pd (PPh 3) 4 (0.28 g, 0.24 mmol), K 2 CO 3 (3.33 g, 24.06mmol) in (3.7 g, 8.02 mmol), THF ( 100 ml) and H ₂ O (50 ml) were used to obtain 3.36 g (yield: 74%) of the product.

3. P-3-3 Synthetic example

Core 3 (4 g, 9.72 mmol ) sub 1-27 (2.34 g, 9.72 mmol), Pd (PPh 3) 4 (0.34 g, 0.29 mmol), K 2 CO 3 (4.03 g, 29.17 mmol) in, THF ( 80 ml) and H ₂ O (40 ml) were used to obtain 3.24 g (yield: 68%) of the product.

4. P-4-8 Synthetic example

Core 4 (2.2 g, 4.75 mmol ) in sub 1-43 (1.17 g, 4.75 mmol ), Pd (PPh 3) 4 (0.16 g, 0.14 mmol), K 2 CO 3 (1.97 g, 14.24 mmol), THF ( 50 ml) and H ₂ O (20 ml) were obtained, and 1.81 g (yield: 70%) of the product was obtained using the above synthesis method of P-1-1.

5. P-5-7 Synthetic example

Sub 1-53 (1.27 g, 4.38 mmol ), Pd (PPh 3) 4 (0.15 g, 0.13 mmol), K 2 CO 3 (1.81 g, 13.13 mmol) in Core 5 (1.80 g, 4.38 mmol ), THF ( 50 ml) and H ₂ O (20 ml) were obtained, 2.13 g (yield: 90%) of the product was obtained using the above synthesis method of P-1-1.

6. P-6-3 Synthetic example

Core 6 (2.50 g, 6.08 mmol ) in sub 1-47 (2.24 g, 6.08 mmol ), Pd (PPh 3) 4 (0.21 g, 0.18 mmol), K 2 CO 3 (2.52 g, 18.23 mmol), THF ( 60 ml) and H ₂ O (30 ml) were used to obtain 3.07 g (yield: 82%) of the product.

7. P-7-6 Synthetic example

Core 7 (1.70 g, 3.68 mmol ) in sub 1-39 (1.17 g, 3.68 mmol ), Pd (PPh 3) 4 (0.13 g, 0.11 mmol), K 2 CO 3 (1.53 g, 11.05 mmol), THF ( 50 ml) and H ₂ O (20 ml) were used to obtain 1.93 g (yield: 85%) of the product.

8. P-8-11 Synthetic example

Sub 1-61 (1.28 g, 4.55 mmol ), Pd (PPh 3) 4 (0.16 g, 0.14 mmol), K 2 CO 3 (1.89 g, 13.65 mmol) in Core 8 (2.10 g, 4.55 mmol ), THF ( 50 ml) and H ₂ O (20 ml) were used to obtain 2.27 g (yield: 86%) of the product.

9. P-9-10 Synthetic example

Core 9 (3 g, 7.29 mmol ) in sub 1-57 (2.53 g, 7.29 mmol ), Pd (PPh 3) 4 (0.25 g, 0.22 mmol), K 2 CO 3 (3.02 g, 21.88 mmol), THF ( 50 ml) and H ₂ O (20 ml) were used to obtain 3.95 g (yield: 91%) of the product.

10. P-10-14 Synthetic example

Core 10 (2.60 g, 6.32 mmol ) in sub 1-60 (1.84 g, 6.32 mmol ), Pd (PPh 3) 4 (0.22 g, 0.19 mmol), K 2 CO 3 (2.62 g, 18.96 mmol), THF ( 50 ml) and H ₂ O (20 ml) were used to obtain 3.04 g (yield: 89%) of the product.

[Table 3]

Evaluation of manufacturing of organic electric device

[Example 1] Production test of red organic light emitting device

First, on the ITO layer (anode) formed on the glass substrate, N ¹ - (naphthalen-2-yl) -N ⁴ and N ⁴ -bis (4- (naphthalen- ) -N ¹ -phenylbenzene-1,4-diamine (abbreviated as 2-TNATA) was formed by vacuum deposition to a thickness of 60 nm. Subsequently, 4,4-bis [N- (1-naphthyl) -N-phenylamino] biphenyl (hereinafter abbreviated as -NPB) was vapor-deposited as a hole transport compound on the film to a thickness of 60 nm to form a hole transport layer . (PQ) ₂ Ir (acac) [Bis (1-phenylisoquinoline) iridium (III) acetylacetonate (III)] was used as a host on the hole transport layer as the host compound P- ] Was doped at a weight ratio of 95: 5 to deposit a light emitting layer with a thickness of 30 nm on the hole transporting layer. ((1,1'-biphenyl) -4-olato) bis (2-methyl-8-quinolinolato) aluminum (hereinafter abbreviated as BAlq) was vacuum deposited as a hole blocking layer to a thickness of 10 nm, (8-hydroxyquinoline) aluminum (hereinafter abbreviated as Alq ₃ ) was deposited to a thickness of 40 nm. Thereafter, LiF, an alkali metal halide, was deposited as an electron injection layer to a thickness of 0.2 nm, and then Al was deposited to a thickness of 150 nm as a cathode to produce an organic electroluminescence device.

[ Example  2] to [ Example  50] Red organic light emitting device

Except that one of the compounds P-1-2 to P-10-20 according to one embodiment of the present invention described in the following Table 4 was used instead of the compound P-1-1 of the present invention as a host material of the light emitting layer. An organic electroluminescent device was prepared in the same manner as in Example 1.

[Comparative Example 1] to [Comparative Example 5] Red organic light emitting element

An organic electroluminescence device was prepared in the same manner as in Example 1, except that one of the following Comparative Compounds A to E was used instead of the compound P-1-1 of the present invention as a host material in the light emitting layer.

&Lt; Comparative Compound A > < Comparative Compound B >

&Lt; Comparative Compound C > < Comparative Compound D > < Comparative Compound E &

The electroluminescence (EL) characteristics of the organic electroluminescence devices of Examples 1 to 50 and Comparative Examples 1 to 5 thus prepared were measured by PR-650 of photoresearch by applying a forward bias DC voltage, Results The T95 lifetime was measured with a lifetime measuring device manufactured by McAfee Inc. at a reference luminance of 2500 cd / m ² . Table 4 shows device fabrication and evaluation results thereof.

[Table 4]

As can be seen from the results of Table 4, it can be seen that the organic electroluminescent device using the organic electroluminescent device material of the present invention as a phosphorescent host can remarkably improve the luminous efficiency, the low driving voltage and the lifetime.

That is, CBP (Comparative Compound A), which is a commonly used host material in device manufacturing, and Comparative Compound C, in which Dibenzothiophen is conjugated to naphthalene rather than Bebq ₂ (Comparative Compound B), showed better device results. Dibenzothiophen showed quinoline The comparative compound D and the comparative compound E bonded together show a lower driving voltage and higher efficiency than the comparative compound C to which naphthalene was bonded. In addition, the comparative compound D and the comparative compound E in which the quinoline is bonded to the heterocycle such as Dibenzothiophen or Cabazole are different in bonding positions, and thus the characteristics of the compound and the result of the device are different. This suggests that the characteristics may vary depending on the position where the heterocyclic compound is bonded to the quinoline and the substitution position of the nitrogen.

Compounds of the present invention in which the substitution position of nitrogen of quinoline and the junction position of quinoline and heterocycle (substitution position of N) are similar to comparative compound E but the hetero element is sulfur (S) or oxygen (O) Compared with the compounds A to E, excellent device results were obtained. This suggests that the characteristics of the compound and the result of the device are significantly different depending on the kind of the hetero element.

Among the compounds of the present invention, compounds represented by Formulas 1-1 to 1-4 wherein R ¹⁰ and R ^11, or R ²² and R ^{23 form} a ring exhibit the best element results, Can be described as having higher thermal stability and an energy level suitable for improving the energy balance within the device.

While the present invention has been described with reference to exemplary embodiments, it is to be understood that the invention is not limited to the disclosed exemplary embodiments. Accordingly, the embodiments disclosed herein are intended to be illustrative rather than limiting, and the spirit and scope of the present invention is not limited by these embodiments. The scope of protection of the present invention should be construed according to the following claims, and all the techniques within the scope of the same should be construed as being included in the scope of the present invention.

100: organic electric element 110: substrate
120: first electrode 130: hole injection layer
140: Hole transport layer 141: Buffer layer
150: light emitting layer 151: light emitting auxiliary layer
160: electron transport layer 170: electron injection layer
180: second electrode

Claims (11)

A compound represented by the following formula (1):
&Lt; Formula 1 >

&Lt; Formula 2 >< EMI ID =

In the above formulas,
A is one of the formulas (2) to (4)
X is -O- or -S-,
R ² to R ²³ independently of one another are hydrogen; heavy hydrogen; halogen; An aryl group of C ₆ -C ₆₀ ; A fluorenyl group; Heterocyclic group of _{O, N, S, C 2} -C 60 containing at least one heteroatom selected from the group consisting of Si and P; A C ₁ -C ₅₀ alkyl group; A fused ring group of a C ₆ -C ₆₀ aromatic ring and a C ₃ -C ₆₀ aliphatic ring; An alkenyl group of C ₂ -C ₂₀ ; A C ₁ -C ₃₀ alkoxyl group; And C ₆ -C ₃₀ aryloxy groups, and R ² to R ²³ are independently of each other, adjacent groups may be bound to each other to form optionally one or more aromatic or heteroaromatic rings, ,
R ¹ is

or

ego,
L &^lt; ¹ &gt; is a single bond; C ₆ -C ₆₀ arylene groups; A fluorenylene group; And a C ₂ -C ₆₀ heteroarylene group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P,
L ² is a C ₆ -C ₆₀ trivalent arylene group; A trivalent fluorenylene group; And a C ₂ -C ₆₀ trivalent heteroarylene group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P,
Ar ¹ and Ar ² are, independently of each other, a C ₆ -C ₆₀ aryl group; A fluorenyl group; A fused ring group of a C ₃ -C ₆₀ aliphatic ring and a C ₆ -C ₆₀ aromatic ring; A C ₂ -C ₆₀ heterocyclic group containing at least one heteroatom in the group consisting of O, N, S, Si and P; And -L'-N (R _a ) (R _b );
L 'is a single bond; C ₆ -C ₆₀ arylene groups; A fluorenylene group; A fused ring group of a C ₃ -C ₆₀ aliphatic ring and a C ₆ -C ₆₀ aromatic ring; And a C ₂ -C ₆₀ heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P, and R _a and R _b are independently selected from the group consisting of A C ₆ -C ₆₀ aryl group; A fluorenyl group; A fused ring group of a C ₃ -C ₆₀ aliphatic ring and a C ₆ -C ₆₀ aromatic ring; And a C ₂ -C ₆₀ heterocyclic group containing at least one heteroatom in the group consisting of O, N, S, Si and P;
Herein, each of the aryl group, the fluorenyl group, the heterocyclic group, the fused ring group, the alkyl group, the alkenyl group, the alkoxyl group, the aryloxy group, the arylene group, the heteroarylene group and the fluorenylene group may be deuterium; halogen; A silane group; Siloxyl group; Boron group; Germanium group; Cyano; A nitro group; An alkyl thio group of C ₁ -C ₂₀ ; A C ₁ -C ₂₀ alkoxyl group; A C ₁ -C ₂₀ alkyl group; An alkenyl group of C ₂ -C ₂₀ ; A C ₂ -C ₂₀ alkynyl group; C ₆ -C ₂₀ An aryl group; A C ₆ -C ₂₀ aryl group substituted by deuterium; A fluorenyl group; A C ₂ -C ₂₀ heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P; A C ₃ -C ₂₀ cycloalkyl group; An arylalkyl group of C ₇ -C ₂₀ ; Aryl, and C ₈ -C ₂₀ alkenyl group of; may be further substituted with one or more substituents selected from the group consisting of and, and, in the case where each of these substituents are adjacent, they bond to one another to form a ring. The method according to claim 1,
The compound of formula (1) is represented by one of the following formulas (5) to (10):
&Lt; Formula 5 >< EMI ID =

&Lt; Formula 8 &gt;&lt; EMI ID =

In the general formulas (5) to (10), X and R ¹ to R ²³ are the same as defined in claim 1. The method according to claim 1,
(1) is represented by one of the following formulas (1-1) to (1-4):
&Lt; Formula 1-1 >< Formula 1-2 >< Formula 1-3 &

In Formulas 1-1 to 1-4, X, R ¹ to R ⁹ and R ¹⁸ to R ²¹ are the same as defined in claim 1,
R ²⁴ to R ²⁷ independently from each other are hydrogen; heavy hydrogen; halogen; An aryl group of C ₆ -C ₆₀ ; A fluorenyl group; Heterocyclic group of _{O, N, S, C 2} -C 60 containing at least one heteroatom selected from the group consisting of Si and P; A C ₁ -C ₅₀ alkyl group; A fused ring group of a C ₆ to C ₆₀ aromatic ring and a C _{3 to} C ₆₀ aliphatic ring; An alkenyl group of C ₂ -C ₂₀ ; A C ₁ -C ₃₀ alkoxyl group; And a C ₆ -C ₃₀ aryloxy group. The method according to claim 1,
A compound characterized by being one of the following compounds:

. A first electrode; A second electrode; And an organic material layer disposed between the first electrode and the second electrode,
Wherein the organic material layer contains the compound of any one of claims 1 to 4. 6. The method of claim 5,
The compound is contained in the light-emitting layer of the organic material layer,
Wherein the compound is contained as a single component or as a component of a mixture of two or more components. The method according to claim 6,
Wherein the compound is used as a phosphorescent host material of the light emitting layer. 6. The method of claim 5,
Further comprising a light-efficiency-improvement layer formed on at least one side of the one surface of the first electrode and the second electrode opposite to the organic material layer. 6. The method of claim 5,
Wherein the organic material layer is formed by a spin coating process, a nozzle printing process, an inkjet printing process, a slot coating process, a dip coating process or a roll-to-roll process. A display device comprising the organic electroluminescent device of claim 5; And
And a control unit for driving the display device. 11. The electronic device according to claim 10, wherein the organic electroluminescent device is at least one of an organic electroluminescent device, an organic solar cell, an organophotoreceptor, an organic transistor, and a monochromatic or white illumination device.

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